


A Convention To Remember

by Salacious_Sovereign



Series: Commissioned Pieces [1]
Category: Original Work
Genre: Awkward First Times, Commissioned Work, Conventions, F/M, Oral Sex, Unattractive People Having Sex
Language: English
Status: In-Progress
Published: 2021-03-04
Updated: 2021-03-04
Packaged: 2021-03-18 16:28:35
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,090
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29371605
Author URL: https://archiveofourown.org/users/Salacious_Sovereign/pseuds/Salacious_Sovereign
Summary: Set to lose their virginities, two unpopular nerds meet up at a convention to awkward results.A commissioned story.
Relationships: Original Female Character/Original Male Character
Series: Commissioned Pieces [1]
Series URL: https://archiveofourown.org/series/2174463





	A Convention To Remember

"This might not be the best idea, Randal..." Cindy's nasally voice trailed off, feeling a bit awkward at her current situation.

Her best friend Randal stood across from her. A portly boy with a bad case of acne, he wasn't a looker in any sense of the word. But he was her closest friend, even if this was the first time they were meeting in person, and she'd never let something as shallow as looks get in the way of that.

But that was a bit more... difficult to keep in mind when they were both naked in a hotel room.

Seeing his flabby, unfit, and hairy body in front of her wasn't exactly the sort of person she thought she'd be seeing for her first sexual experience, but beggars can't be choosers, and Cindy was more than aware she fit firmly into the 'beggars' category.

"Oh come on Cindy!" Randal said, his plump form jiggling just slightly with the movement, "you were the one who offered in the first place!"

That was true enough. Cindy, with her bone-thin body and need for braces for the next four years at least, knew she'd never get a boy under normal circumstances, and had offered to deal with each other's virginities once and for all, meeting for the first time in person at a mid-sized anime convention. It had seemed a good idea at the time, and as she glanced at her body in the nearby mirror, she resolved that as nervous as she might be, it was still her best bet at having sex in the next decade without paying for it.

"I know, I know... Okay, how do you want to start this?"

At that the boy began to tap a finger on his chin in thought. "How about a blowjob? All the porn I've ever seen starts with a blowjob!"

While Cindy wasn't sure they should be taking experience from porn, it wasn't like they had anything else to base off of. So she seated him on the edge of the bed while she sat on her knees in front of him, thankful for the carpeted floor and rug underneath. Looking at his spread legs, the only thing keeping the flab from covering his crotch entirely, she got a close look at her very first real-life penis. It was shocking to say the least, to see this thing she'd so desperately coveted for years now was finally within reach.

She reached out and grabbed it shakily, and recalling her own experiences with porn, stuck out her tongue and licked around the tip. It was a bit more... pungent than she was expecting, and she could definitely taste something that wasn't exactly sweat on her friend's shaft, but she steeled herself and licked around the tip, taking her time to get used to the slightly strong taste on her friend's shaft.

She could hear him above her, heaving heavily and muttering "oh my god, oh my god" under his breath, but endeavored to ignore it for now. She was definitely in no position to judge, as she wasn't sure she'd be any better once they were actually having sex.

Cindy decided it’d be time to move further down the shaft, and so she wrapped her lips around the tip and pushed further downwards. As she moved, she heard Randal give off a sharp hiss, and quickly pulled off and looked up, the wince on his face worrying her.

“Did I mess up?” she asked in a concerned tone, hand still gripping his penis.

“Y-Yeah, you were doing okay, just please be careful with your braces?” he said awkwardly, torn between the brief pain on his most sensitive part and the elation of a girl holding his dick.

Cindy could feel her cheeks heat up as embarrassment filled her. “Okay, s-sure Randal, I’ll be more careful.” she responded, and looked back towards the pulsing cock in her grip. Moving down once more, she engulfed the head with her lips and gave it a few licks, putting in some extra effort as an apology to her friend.

She stayed for a few seconds before deciding to move back down as she was originally planning before her damned braces messed things up. As she moved, Cindy moved her tongue just a little bit on the underside of his cock, getting hints of that strong taste she was beginning to associate with the word boy.

It was exhilarating.

The scent of his musk filling her nostrils, the tang of man coating her taste buds, it was so very naughty and wild that she already felt like she’d lost her virginity! To be able to tangibly taste her womanly-ness growing, to know that she wasn’t a little girl anymore! That she could suck on a boy’s dick and have him like it, braces be damned! She was a woman now, screw what Vanessa had to say-

Her thoughts were cut off by the squeal of her friend and warm goo hitting the back of her throat.

Cindy began to splutter, not expecting that first jet to go off inside her mouth, but tightened her lips around the cock to not let any out. She silently coughed as the pulsating organ fired streams into her mouth, her inexperience and surprise making the few shots feel like a mouthful.

But after what felt like at least ten minutes but was probably a couple of seconds, it stopped, and she was able to breath enough to get ahold of its taste. Salty, warm goo was a very weird flavor for Cindy, and she wasn’t entirely sure she liked it. But she wanted to be a woman damnit, and began to swallow some down.

...Only for her already irritated throat to reject that notion and make her cough harder, accidentally spitting up the cum all over her front. She saw it run down her rail-thin body with conflicting disappointment and relief.

As she calmed her gag reflex down, her friend spoke. “That was amazing Cindy! God, I can’t tell you how great you were, besides the braces thing of course, but it doesn’t even matter because-”

She cut Randal off with a gentle slap to his belly, and looked up at him. With his cum dripping down her chin and chest and tears at the edge of her vision from gagging, she told him in a hoarse voice “Let’s go to the next part, okay?”

And Cindy knew the unashamed eagerness she saw was certainly mirrored on her own.


End file.
